Expedient five-step synthesis of SIB-1508Y from natural nicotine

被引：30

作者：

Wagner, Florence F. ^{[1
]}

Comins, Daniel L. ^{[1
]}

机构：

[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 22期

关键词：

D O I：

10.1021/jo0616052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Altinicline (SIB-1508Y), an anti-Parkinson's agent, was prepared in five steps from natural nicotine in 32% overall yield via a regioselective substitution of the pyridine ring of (S)-nicotine.

引用

页码：8673 / 8675

页数：3

共 14 条

[1] A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y)
Bleicher, LS
Cosford, NDP
Herbaut, A
McCallum, JS
McDonald, IA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) : 1109 - 1118
[2] COMINS DL, Patent No. 7067672
[3] COMINS DL, Patent No. 10925516
[4] COMINS DL, Patent No. 60787116
[5] CORNINS DL, 2006, TETRAHEDRON LETT, V47, P1449
[6] Cosford N D, 2000, Pharm Acta Helv, V74, P125, DOI 10.1016/S0031-6865(99)00024-2
[7] (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y): A novel anti-Parkinsonian agent with selectivity for neuronal nicotinic acetylcholine receptors
Cosford, NDP
Bleicher, L
Herbaut, A
McCallum, JS
Vernier, JM
Dawson, H
Whitten, JP
Adams, P
ChavezNoriega, L
Correa, LD
Crona, JH
Mahaffy, LS
Menzaghi, F
Rao, TS
Reid, R
Sacaan, AI
Santori, E
Stauderman, KA
Whelan, K
Lloyd, GK
McDonald, IA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) : 3235 - 3237
[8] Enantioselective reduction of heteroaromatic β,γ-unsaturated ketones as an alternative to allylboration of aldehydes.: Application:: asymmetric synthesis of SIB-1508Y
Felpin, FX
Bertrand, MJ
Lebreton, J
[J]. TETRAHEDRON, 2002, 58 (37) : 7381 - 7389
[9] The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine:: a key intermediate for the preparation of SIB-1508Y
Felpin, FX
Vo-Thanh, G
Villiéras, J
Lebreton, J
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (08) : 1121 - 1124
[10] Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives
Février, FC
Smith, ED
Comins, DL
[J]. ORGANIC LETTERS, 2005, 7 (24) : 5457 - 5460

← 1 2 →